CN106366152A - Method of extracting asiaticoside from centella asiatica - Google Patents
Method of extracting asiaticoside from centella asiatica Download PDFInfo
- Publication number
- CN106366152A CN106366152A CN201610726900.3A CN201610726900A CN106366152A CN 106366152 A CN106366152 A CN 106366152A CN 201610726900 A CN201610726900 A CN 201610726900A CN 106366152 A CN106366152 A CN 106366152A
- Authority
- CN
- China
- Prior art keywords
- asiaticoside
- herba centellae
- extract
- ethanol
- mixed liquor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- WYQVAPGDARQUBT-XCWYDTOWSA-N asiaticoside Natural products O=C(O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@H](O)[C@H](O)[C@H](O[C@H]3[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O3)[C@@H](CO)O2)O1)[C@@]12[C@@H]([C@@H](C)[C@H](C)CC1)C=1[C@](C)([C@@]3(C)[C@@H]([C@@]4(C)[C@H]([C@@](CO)(C)[C@@H](O)[C@H](O)C4)CC3)CC=1)CC2 WYQVAPGDARQUBT-XCWYDTOWSA-N 0.000 title claims abstract description 46
- 229940022757 asiaticoside Drugs 0.000 title claims abstract description 46
- QCYLIQBVLZBPNK-UHFFFAOYSA-N asiaticoside A Natural products O1C(C(=O)C(C)C)=CC(C)C(C2(C(OC(C)=O)CC34C5)C)C1CC2(C)C3CCC(C1(C)C)C45CCC1OC1OCC(O)C(O)C1O QCYLIQBVLZBPNK-UHFFFAOYSA-N 0.000 title claims abstract description 46
- WYQVAPGDARQUBT-FGWHUCSPSA-N Madecassol Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)OC[C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)OC(=O)[C@]12CC[C@H]([C@@H]([C@H]1C=1[C@@]([C@@]3(CC[C@H]4[C@](C)(CO)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC=1)C)(C)CC2)C)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O WYQVAPGDARQUBT-FGWHUCSPSA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 17
- 244000146462 Centella asiatica Species 0.000 title abstract description 4
- 235000004032 Centella asiatica Nutrition 0.000 title abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 22
- -1 rare earth salt Chemical class 0.000 claims abstract description 20
- 239000000284 extract Substances 0.000 claims abstract description 18
- 239000000287 crude extract Substances 0.000 claims abstract description 14
- 239000011347 resin Substances 0.000 claims abstract description 14
- 229920005989 resin Polymers 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 8
- 238000004064 recycling Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims abstract 8
- 238000010828 elution Methods 0.000 claims description 12
- 229910002651 NO3 Inorganic materials 0.000 claims description 7
- 238000013461 design Methods 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 5
- 238000000605 extraction Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000001035 drying Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 150000002910 rare earth metals Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 3
- 229930182493 triterpene saponin Natural products 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 2
- 241000167550 Centella Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 2
- 229910000333 cerium(III) sulfate Inorganic materials 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical group Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- YWECOPREQNXXBZ-UHFFFAOYSA-N praseodymium(3+);trinitrate Chemical compound [Pr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YWECOPREQNXXBZ-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229930182490 saponin Natural products 0.000 description 2
- 150000007949 saponins Chemical class 0.000 description 2
- 235000017709 saponins Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- OBOSXEWFRARQPU-UHFFFAOYSA-N 2-n,2-n-dimethylpyridine-2,5-diamine Chemical compound CN(C)C1=CC=C(N)C=N1 OBOSXEWFRARQPU-UHFFFAOYSA-N 0.000 description 1
- 241000208173 Apiaceae Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910003317 GdCl3 Inorganic materials 0.000 description 1
- 241000196322 Marchantia Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- MKNZSAIPAVSJSI-UHFFFAOYSA-N [Tb].S(O)(O)(=O)=O Chemical compound [Tb].S(O)(O)(=O)=O MKNZSAIPAVSJSI-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- JXSVIVRDWWRQRT-UYDOISQJSA-N asiatic acid Chemical compound C1[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C JXSVIVRDWWRQRT-UYDOISQJSA-N 0.000 description 1
- 229940011658 asiatic acid Drugs 0.000 description 1
- LBGFKBYMNRAMFC-PYSQTNCISA-N asiatic acid Natural products C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@]2(C)[C@H]1C)C(=O)O LBGFKBYMNRAMFC-PYSQTNCISA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- DVENVBCPDCQQGD-UHFFFAOYSA-N dysprosium(3+);trinitrate Chemical compound [Dy+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O DVENVBCPDCQQGD-UHFFFAOYSA-N 0.000 description 1
- FLWXWKDFOLALOB-UHFFFAOYSA-H dysprosium(3+);trisulfate Chemical compound [Dy+3].[Dy+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FLWXWKDFOLALOB-UHFFFAOYSA-H 0.000 description 1
- BOXVSFHSLKQLNZ-UHFFFAOYSA-K dysprosium(iii) chloride Chemical compound Cl[Dy](Cl)Cl BOXVSFHSLKQLNZ-UHFFFAOYSA-K 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- YBYGDBANBWOYIF-UHFFFAOYSA-N erbium(3+);trinitrate Chemical compound [Er+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YBYGDBANBWOYIF-UHFFFAOYSA-N 0.000 description 1
- SYDXSHCNMKOQFW-UHFFFAOYSA-H erbium(3+);trisulfate Chemical compound [Er+3].[Er+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O SYDXSHCNMKOQFW-UHFFFAOYSA-H 0.000 description 1
- HDGGAKOVUDZYES-UHFFFAOYSA-K erbium(iii) chloride Chemical compound Cl[Er](Cl)Cl HDGGAKOVUDZYES-UHFFFAOYSA-K 0.000 description 1
- CLXOLTFMHAXJST-UHFFFAOYSA-N esculentic acid Natural products C12CC=C3C4CC(C)(C(O)=O)CCC4(C(O)=O)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(CO)C CLXOLTFMHAXJST-UHFFFAOYSA-N 0.000 description 1
- GAGGCOKRLXYWIV-UHFFFAOYSA-N europium(3+);trinitrate Chemical compound [Eu+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GAGGCOKRLXYWIV-UHFFFAOYSA-N 0.000 description 1
- NNMXSTWQJRPBJZ-UHFFFAOYSA-K europium(iii) chloride Chemical compound Cl[Eu](Cl)Cl NNMXSTWQJRPBJZ-UHFFFAOYSA-K 0.000 description 1
- WLYAEQLCCOGBPV-UHFFFAOYSA-N europium;sulfuric acid Chemical compound [Eu].OS(O)(=O)=O WLYAEQLCCOGBPV-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 1
- XKJJKZIBLKQSLH-UHFFFAOYSA-N gadolinium;nitric acid Chemical compound [Gd].O[N+]([O-])=O XKJJKZIBLKQSLH-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- JTZUUBNBNBFJCX-UHFFFAOYSA-N holmium sulfuric acid Chemical compound [Ho].S(O)(O)(=O)=O JTZUUBNBNBFJCX-UHFFFAOYSA-N 0.000 description 1
- WDVGLADRSBQDDY-UHFFFAOYSA-N holmium(3+);trinitrate Chemical compound [Ho+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O WDVGLADRSBQDDY-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 1
- VQEHIYWBGOJJDM-UHFFFAOYSA-H lanthanum(3+);trisulfate Chemical compound [La+3].[La+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VQEHIYWBGOJJDM-UHFFFAOYSA-H 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- PRAUVHZJPXOEIF-AOLYGAPISA-N madecassic acid Chemical compound C1[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]2[C@H](O)C[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C PRAUVHZJPXOEIF-AOLYGAPISA-N 0.000 description 1
- 229940011656 madecassic acid Drugs 0.000 description 1
- BUWCHLVSSFQLPN-UHFFFAOYSA-N madecassic acid Natural products CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C5CCC34C)C(=O)O)C2C1C)C(=O)OC6OC(COC7OC(CO)C(OC8OC(C)C(O)C(O)C8O)C(O)C7O)C(O)C(O)C6O BUWCHLVSSFQLPN-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CFYGEIAZMVFFDE-UHFFFAOYSA-N neodymium(3+);trinitrate Chemical compound [Nd+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CFYGEIAZMVFFDE-UHFFFAOYSA-N 0.000 description 1
- OJSWEKSDNUORPG-UHFFFAOYSA-H neodymium(3+);trisulfate Chemical compound [Nd+3].[Nd+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OJSWEKSDNUORPG-UHFFFAOYSA-H 0.000 description 1
- ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- LHBNLZDGIPPZLL-UHFFFAOYSA-K praseodymium(iii) chloride Chemical compound Cl[Pr](Cl)Cl LHBNLZDGIPPZLL-UHFFFAOYSA-K 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LVSITDBROURTQX-UHFFFAOYSA-H samarium(3+);trisulfate Chemical compound [Sm+3].[Sm+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LVSITDBROURTQX-UHFFFAOYSA-H 0.000 description 1
- BHXBZLPMVFUQBQ-UHFFFAOYSA-K samarium(iii) chloride Chemical compound Cl[Sm](Cl)Cl BHXBZLPMVFUQBQ-UHFFFAOYSA-K 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000346 scandium sulfate Inorganic materials 0.000 description 1
- DFCYEXJMCFQPPA-UHFFFAOYSA-N scandium(III) nitrate Inorganic materials [Sc+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O DFCYEXJMCFQPPA-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YJVUGDIORBKPLC-UHFFFAOYSA-N terbium(3+);trinitrate Chemical compound [Tb+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YJVUGDIORBKPLC-UHFFFAOYSA-N 0.000 description 1
- GFISHBQNVWAVFU-UHFFFAOYSA-K terbium(iii) chloride Chemical compound Cl[Tb](Cl)Cl GFISHBQNVWAVFU-UHFFFAOYSA-K 0.000 description 1
- LLZBVBSJCNUKLL-UHFFFAOYSA-N thulium(3+);trinitrate Chemical compound [Tm+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O LLZBVBSJCNUKLL-UHFFFAOYSA-N 0.000 description 1
- NEEAOWXTIOQDFM-UHFFFAOYSA-H thulium(3+);trisulfate Chemical compound [Tm+3].[Tm+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O NEEAOWXTIOQDFM-UHFFFAOYSA-H 0.000 description 1
- ILOTUXNTERMOJL-UHFFFAOYSA-K thulium(iii) chloride Chemical compound Cl[Tm](Cl)Cl ILOTUXNTERMOJL-UHFFFAOYSA-K 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- PYOOBRULIYNHJR-UHFFFAOYSA-K trichloroholmium Chemical compound Cl[Ho](Cl)Cl PYOOBRULIYNHJR-UHFFFAOYSA-K 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- OOTXFYSZXCPMPG-BMYLZFHVSA-N ursane Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5[C@H]4CC[C@@H]3[C@]21C OOTXFYSZXCPMPG-BMYLZFHVSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- KUBYTSCYMRPPAG-UHFFFAOYSA-N ytterbium(3+);trinitrate Chemical compound [Yb+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O KUBYTSCYMRPPAG-UHFFFAOYSA-N 0.000 description 1
- KVCOOBXEBNBTGL-UHFFFAOYSA-H ytterbium(3+);trisulfate Chemical compound [Yb+3].[Yb+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O KVCOOBXEBNBTGL-UHFFFAOYSA-H 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
- BXJPTTGFESFXJU-UHFFFAOYSA-N yttrium(3+);trinitrate Chemical compound [Y+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O BXJPTTGFESFXJU-UHFFFAOYSA-N 0.000 description 1
- RTAYJOCWVUTQHB-UHFFFAOYSA-H yttrium(3+);trisulfate Chemical compound [Y+3].[Y+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RTAYJOCWVUTQHB-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a method of extracting asiaticoside from centella asiatica. The method includes the steps of: 1) crushing the centella asiatica, and performing reflux extraction with a 60-70% ethanol solution, filtering an extract liquid to obtain a filtrate, recycling the solvent from the filtrate, adding water at 40-50 DEG C to dissolve the extract liquid to obtain a crude extract liquid; 2) adding rare earth salt to the crude extract liquid, and uniformly mixing and stirring the mixed liquid; 3) enabling the mixed liquid to pass through a X-5 macroporous resin column, wherein the mixed liquid is washed to colorless by water and then is eluted by ethanol being 50-70% in volume concentration, and collecting an eluant, recycling the ethanol and drying the eluant to obtain the asiaticoside. The method is high in purity and yield of the asiaticoside.
Description
Technical field
The invention belongs to technical field of biological extraction and in particular to a kind of from Herba Centellae extract asiaticoside method.
Background technology
Herba Centellae (centella asiatica (l.) urban) is Umbelliferae Herba Centellae tree plant, because its leaf exactly likes horse
Shoes or half copper coin, so also known as Herba Calthae Membranaceae, Herba Glechomae etc., among the people also have place to be called pennyroyal mint, marchantia grass etc..Accumulated snow
Applicating history in the traditional medicine field of many countries and regions for the grass is long, China's Chinese medicine to for oral administration of Herba Centellae and
The existing bimillennium history of external, is recorded by Shennong's Herbal one book earliest.Record according to Compendium of Material Medica, Herba Centellae bitter in the mouth,
Pungent, cold in nature, nontoxic, return liver,spleen,kidney, stomach, its effect is promoting blood circulation, reducing swelling and alleviating pain, and has heat-clearing and toxic substances removing, diuresis etc..Herba Centellae
Chemical composition mainly have triterpeness, flavonoid, polyacetylene alkenes and volatile oil etc..Triterpeness mainly have triterpene saponin, such as
Asiaticoside, asiaticoside etc., and triterpene acids, such as asiatic acid, Madecassic acid etc..The chemical composition of Herba Centellae
In, Triterpene saponins are that research is earliest, a biological activity research big class component the most deep.Asiatic centella total saponins are mainly by amassing
Asiaticoside and asiaticoside composition, they belong to the pentacyclic triterpene saponin of Ursane, be Herba Centellae pharmacologically active
Main component.Asiaticoside typically first uses extract by solvents, then carries out purification using the less macroporous resin of average pore size, such as
Hpd-100 (average pore size is 8.5～9.0nm), hpd-300 (average pore size is 5.0～5.5nm), because macroporous resin is to mesh
The absorption of mark composition and screening specific aim are not very strong, and in adsorption process, a lot of impurity can be adsorbed onto in resin voids, and solves
During suction, because hole is less, target component can not desorbing completely, therefore, the yield of asiaticoside after purification and purity are equal
Not high.
Content of the invention
Present invention solves the technical problem that being to provide a kind of method extracting asiaticoside from Herba Centellae, the method is extracted
The asiaticoside yield obtaining is big, and purity is high.
The technical scheme that the present invention provides is to provide a kind of method extracting asiaticoside from Herba Centellae, walks including following
Rapid:
1) Herba Centellae is pulverized, with 60～70v% ethanol solution reflux, extract, extracting solution is filtered, filtrate recycling design,
Plus 40 again～50 DEG C of water dissolutioies, obtain crude extract；
2) add rare-earth salts mixing toward crude extract, stir evenly, obtain mixed liquor；
3) by x-5 model macroporous resin column on mixed liquor, first it is washed to colourless, then use volumetric concentration to be 35～45v%
Ethanol elution, thin layer chromatography tracing detection, collect the ethanol elution containing target component, reclaim ethanol, be dried, obtain Herba Centellae
Glycosides.
Step 1) in, the consumption of ethanol is 10～20 times of Herba Centellae weight, reflux, extract, 1～3 time, 1～3h every time.
Volumetric concentration is 60～70% ethanol triterpene substance that can fully dissolve in Herba Centellae, including the total soap of triterpeness
Glycosides and triterpene acid.Asiatic centella total saponins are many due to being often combined with most glycan molecules, hydroxy number in their molecule,
Certain hydrophilic can be shown, but hydrophilic is not strong, be slightly soluble in water, and triterpene acids polarity less it is impossible to be dissolved in water
In.Therefore asiaticoside can be helped to dissolve using 40～50 DEG C of warm water, Herba Centellae acid is insoluble in water, to reach
Purpose except Triterpene acids.
Step 2) in, described rare-earth salts is rare earth chloride, rare earth sulfate or rare earth nitrate.Rare earth chloride is permissible
It is lanthanum chloride, cerium chloride, praseodymium chloride, Neodymium chloride, samarium trichloride, Europium chloride, Gadolinium trichloride, terbium chloride, Dysprosium trichloride, Holmium trichloride, chlorination
Erbium, thulium chloride, Ytterbium trichloride, lutecium chloride, Scium chloride (Sc4Cl12) and Yttrium chloride(Y2Cl6)；Rare earth sulfate can be lanthanum sulfate, cerous sulfate, Dipraseodymium trisulfate,
Dineodymium trisulfate, samarium sulphate, europium sulfate, Digadolinium trisulfate, sulphuric acid terbium, Dysprosium sesquisulfate, sulphuric acid holmium, erbium sulfate, thulium sulfate, Ytterbium Sulfate, sulphuric acid lutecium,
Scium sulfate (Sc2(SO4)3) and Yttrium sesquisulfate；Rare earth nitrate can be Lanthanum (III) nitrate, cerous nitrate, praseodymium nitrate, neodymium nitrate, samaric nitrate, europium nitrate, nitric acid
Gadolinium, Terbium nitrate (Tb(NO3)3), Dysprosium trinitrate, holmium nitrate, Erbium trinitrate, thulium nitrate, Ytterbium(III) nitrate., lutecium nitrate, Scium nitrate(Sc(NO3)3) and Yttrium trinitrate.
Oxygen atom on hydroxyl on rare earth element and asiaticoside and asiaticoside, carboxyl formed coordinate bond and, shape
Become chemical affinity, according to hsab theory, because rare earth is hard acid, asiaticoside and asiaticoside are soft bases, because
This, both combinations are not especially to consolidate.
Rare-earth salts accounts for the 0.1～0.5% of mixed liquor gross weight.Now, rare-earth salts can be fully coordinated with target component.
Step 3) in, x-5 model macroporous resin is non-polar resin, and particle diameter is 0.3～1.25mm, and specific surface area is 500
～600m2/ g, average pore size is 29～30nm.Its aperture is far longer than the molecular particle size of asiaticoside.And the ligancy of rare earth
Larger, with its carry out coordinate bond and oxygen-containing functional group number often do not reach its highest ligancy, therefore rare earth also can with big
C in the resin of hole produces crosslinked, to reach the effect of absorption.
In order to ensure the crosslinking of rare earth element and macroporous resin, the upper prop speed of mixed liquor is less, and effect is better, through application
People's many experiments, mixed liquor upper prop speed is 0.5～0.8bv/h, and cross-linking effect is best.
Due to rare earth element and asiaticoside and asiaticoside combination very built on the sand, and asiaticoside and ethanol
Affinity extremely strong it is easy to be eluted by ethanol solution.There is hydroxyl due on three sites of asiaticoside, these three positions again
Point is all that coordination atom is coordinated with rare earth atom, and asiaticoside hydroxyl more than asiaticoside, coordination ability
Higher.Therefore, in eluting, asiaticoside is first eluted.The ethanol being 35～45% using volumetric concentration can preferentially by
Asiaticoside eluting, and it is not mixed into asiaticoside.Elution speed is advisable for 2～2.5bv/h.
Compared with prior art, this method carries out adsorption and desorption, the asiaticoside yield of extraction for target component
Up to more than 95%, high purity more than 99.5%.
Specific embodiment
The present invention is further elaborated for specific examples below, but not as a limitation of the invention.
Following percent is percentage by volume.
Embodiment 1
1) Herba Centellae is pulverized, 60% ethanol solution reflux, extract, of 10 times of Herba Centellae gross weight of addition 1 time, each 1h, will
Extracting solution filter, by filtrate recycling design, then plus 40 DEG C of water dissolutioies, remove filtering residue, obtain final product crude extract；
2) add its weight 0.1% lanthanum chloride to mix toward crude extract, stir evenly, obtain mixed liquor；
3) by x-5 model macroporous resin column on mixed liquor, upper prop speed is 0.5bv/h, is first washed to colourless, then uses body
Long-pending concentration is 35v% ethanol elution, and thin layer chromatography tracing detection collects the ethanol elution containing target component, reclaims ethanol, does
Dry, obtain asiaticoside.
Through hlpc analysis, the response rate of asiaticoside is more than 95.24%, high purity more than 99.50%.
Embodiment 2
1) Herba Centellae is pulverized, 70% ethanol solution reflux, extract, of 20 times of Herba Centellae gross weight of addition 3 times, each 3h, will
Extracting solution merge, filter, by filtrate recycling design, then plus 50 DEG C of water dissolutioies, remove filtering residue, obtain final product crude extract；
2) add its weight 0.5% cerous sulfate to mix toward crude extract, stir evenly, obtain mixed liquor；
3) by x-5 model macroporous resin column on mixed liquor, upper prop speed is 0.8bv/h, is first washed to colourless, then uses body
Long-pending concentration is 45v% ethanol elution, and thin layer chromatography tracing detection collects the ethanol elution containing target component, reclaims ethanol, does
Dry, obtain asiaticoside.
Through hlpc analysis, the response rate of asiaticoside is more than 95.33%, high purity more than 99.58%.
Embodiment 3
1) Herba Centellae is pulverized, 65% ethanol solution reflux, extract, of 15 times of Herba Centellae gross weight of addition 2 times, each 2h, will
Extracting solution merge, filter, by filtrate recycling design, then plus 45 DEG C of water dissolutioies, remove filtering residue, obtain final product crude extract；
2) add its weight 0.2% praseodymium nitrate to mix toward crude extract, stir evenly, obtain mixed liquor；
3) by x-5 model macroporous resin column on mixed liquor, upper prop speed is 0.6bv/h, is first washed to colourless, then uses body
Long-pending concentration is 40v% ethanol elution, and thin layer chromatography tracing detection collects the ethanol elution containing target component, reclaims ethanol, does
Dry, obtain asiaticoside.
Through hlpc analysis, the response rate of asiaticoside is more than 95.18%, high purity more than 99.55%.
Embodiment 4
1) Herba Centellae is pulverized, 70% ethanol solution reflux, extract, of 10 times of Herba Centellae gross weight of addition 3 times, each 1h, will
Extracting solution merge, filter, by filtrate recycling design, then plus 50 DEG C of water dissolutioies, remove filtering residue, obtain final product crude extract；
2) add its weight 0.1% Erbium trichloride to mix toward crude extract, stir evenly, obtain mixed liquor；
3) by x-5 model macroporous resin column on mixed liquor, upper prop speed is 0.5bv/h, is first washed to colourless, then uses body
Long-pending concentration is 45v% ethanol elution, and thin layer chromatography tracing detection collects the ethanol elution containing target component, reclaims ethanol, does
Dry, obtain asiaticoside.
Through hlpc analysis, the response rate of asiaticoside is more than 95.09%, high purity more than 99.63%.
Claims (6)
1. from Herba Centellae extract asiaticoside method it is characterised in that: comprise the following steps:
1) Herba Centellae is pulverized, with 60～70v% ethanol solution reflux, extract, extracting solution is filtered, filtrate recycling design, then plus
40～50 DEG C of water dissolutioies, obtain crude extract；
2) add rare-earth salts mixing toward crude extract, stir evenly, obtain mixed liquor；
3) by x-5 model macroporous resin column on mixed liquor, first it is washed to colourless, then use volumetric concentration to be 35～45v% ethanol
Eluting, thin layer chromatography tracing detection, collect the ethanol elution containing target component, reclaim ethanol, be dried, obtain asiaticoside.
2. according to claim 1 from Herba Centellae extract asiaticoside method it is characterised in that: step 1) in, second
The consumption of alcohol is 10～20 times of Herba Centellae weight, reflux, extract, 1～3 time, 1～3h every time.
3. according to claim 1 from Herba Centellae extract asiaticoside method it is characterised in that: step 2) in, institute
Stating rare-earth salts is rare earth chloride, rare earth sulfate or rare earth nitrate.
4. according to claim 1 from Herba Centellae extract asiaticoside method it is characterised in that: step 2) in, dilute
Earth salt accounts for the 0.1～0.5% of mixed liquor gross weight.
5. according to claim 1 from Herba Centellae extract asiaticoside method it is characterised in that: step 3) in, mix
Conjunction liquid upper prop speed is 0.5～0.8bv/h.
6. according to claim 1 from Herba Centellae extract asiaticoside method it is characterised in that: step 3) in, wash
De- speed is 2～2.5bv/h.
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| CN109320580A (en) * | 2018-10-30 | 2019-02-12 | 天峨县科学技术情报研究所 | A method of extracting asiatic acid from centella |
| CN109320579A (en) * | 2018-10-30 | 2019-02-12 | 天峨县科学技术情报研究所 | The extracting method of Gotu Kola P.E |
| CN114014904A (en) * | 2021-11-19 | 2022-02-08 | 湘南学院 | Method for rapidly preparing high-content asiaticoside from asiatic pennywort herb raw material |
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| CN1244036A (en) * | 1998-07-31 | 2000-02-09 | 西门子公司 | Device and method for forming controllable isolating layer on top of deep channel |
| CN101200487A (en) * | 2007-11-27 | 2008-06-18 | 浙江大学 | Method for preparing asiatic centella total saponins by using macroporous adsorption resin |
| CN102603854A (en) * | 2011-01-25 | 2012-07-25 | 苏州宝泽堂医药科技有限公司 | Method for extracting asiaticoside from asiatic pennywort herb |
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| CN1244036A (en) * | 1998-07-31 | 2000-02-09 | 西门子公司 | Device and method for forming controllable isolating layer on top of deep channel |
| CN101200487A (en) * | 2007-11-27 | 2008-06-18 | 浙江大学 | Method for preparing asiatic centella total saponins by using macroporous adsorption resin |
| CN102603854A (en) * | 2011-01-25 | 2012-07-25 | 苏州宝泽堂医药科技有限公司 | Method for extracting asiaticoside from asiatic pennywort herb |
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| CN109320580A (en) * | 2018-10-30 | 2019-02-12 | 天峨县科学技术情报研究所 | A method of extracting asiatic acid from centella |
| CN109320579A (en) * | 2018-10-30 | 2019-02-12 | 天峨县科学技术情报研究所 | The extracting method of Gotu Kola P.E |
| CN114014904A (en) * | 2021-11-19 | 2022-02-08 | 湘南学院 | Method for rapidly preparing high-content asiaticoside from asiatic pennywort herb raw material |
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